STRUCTURE (I) has been suggested for averufin, a metabolite of Aspergillus versicolor (Vuill.) Tiraboschi.' We have now shown that mutation of this organism, by ultraviolet irradiation of the spores, gives strains producing new metabolites. Three of these are orange optically active compounds m.p.'s 260', 252-254', and 219-5220" for which we suggest structures (11), ( 111) and (IV) respectively.The structural evidence for these compounds, which will be reported fully elsewhere, is based on the following observations and deductions :-(a) All three compounds give the same fully methylated derivative (V) .

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Solid state infrared curves (O‐H and C‐H stretching region) are given for 5, n‐dihydroxyflavones, where n is 2′, 3′, 4′, 6, 7 and 8. In chloroform solution spectra of 3,5‐dihydroxyflavone and 3‐hydroxy‐5‐methoxyflavone, the 3‐OH stretching band appears at 3400 and 3334 cm−1, respectively, indicative of a stronger hydrogen bond in the latter substance. Solid state and solution carbonyl bands are presented for twenty‐six flavone derivatives which contain a hydroxyl, methoxyl or acetoxyl group at the 5‐position. The solution spectra (dioxane or carbon tetrachloride) of fourteen flavone derivatives containing a free 5‐hydroxyl group show carbonyl bands at 1655±2 cm−1. Eleven flavones in which the 5‐hydroxyl is blocked (carbon tetrachloride solution) give spectra with flavone carbonyl bands at 1653±3 cm−1. The high resolution chloroform solution spectrum of 3, 5‐dihydroxyflavone possesses a multi‐peaked carbonyl band with midpoint at 1641 cm−1. The chloroform solution spectrum of 3‐hydroxy‐5‐methoxyflavone has a very strong band at 1616 cm−1, with shoulder at 1646 cm−1. Spectral data of this and a previous paper support the postulate that in 4′‐hydroxyflavone the flavone carbonyl oxygen is the donor atom in an intermolecular hydrogen bond. Certain details of synthesis, and analytical data, are given for 3, 5‐dihydroxyflavone.

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The mass spectra of the phenylhydrazones and 2,4-dinitrophenylhydrazones of orrho substituted benzaldehydes and acetophenones (X = I, Br, CI, OCH,, OH) show characteristic [M -XI+ ions which allow the ortho derivatives to be distinguished from their mefa and pnru isomers. * S. Kagal, unpublished results.